
Vacation rentals in Peekskill
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Top-rated vacation rentals in Peekskill
Guests agree: these stays are highly rated for location, cleanliness, and more.

The Little Cottage in the Woods
The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Little Yellow Cottage New Paltz - Kitchen wash/dry
Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

The Peekskill RiverView House
The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station, the train is loud, as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Unwind in a Bespoke Downtown Studio W Laundry
A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Hiker's nest
This is a cozy room with private forest views and all the basic amenities (small kitchenette). We are located next to the entrance of Mount Beacon park (the free Loop Bus from the station drops you on our corner), a three-minute walk to the trail entrance, and a 25 minute walk to the train station and Main Street. The room is attached to the main house, but you have your own entrance with code access. We live in the main house, so we are here to answer questions or help with your stay.

Hudson River Peaceful Getaway, Explore from here
Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Modern+bright forest escape - near village & train
Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

Hudson Valley Tiny House
If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

Studio in Cornwall
Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited.

Rustic Spa Retreat
10 minute walk to Main Street (many restaurants, cafes, galleries, etc) 10 minute walk to Mt Beacon TrailHead. (It's not a hotel and not on Main Street: it's in a residential neighborhood) Cozy, small space set up for a couple (or solo traveler) looking for a relaxing short escape from "The Real World". A couple days here really feels likes so much longer (especially if you take a steam and a jacuzzi)!
Popular amenities for Peekskill vacation rentals
Other great vacation rentals in Peekskill

Gorgeous Suite w/ Private Entrance

Sweet, stylish cabin in the woods- hiking & more!

Haverstraw Hospitality Suite

Nestled in Nature

Victorian Eclectic

Riverview B&B 2 Miles to West Point

A Lovely Cottage in the Woods

A nice place to getaway
When is the best time to visit Peekskill?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $131 | $125 | $113 | $118 | $153 | $149 | $155 | $165 | $163 | $151 | $125 | $125 |
| Avg. temp | 34°F | 36°F | 43°F | 54°F | 64°F | 73°F | 79°F | 78°F | 71°F | 60°F | 49°F | 40°F |
Frequently Asked Questions
Are there family-friendly house rentals in Peekskill?
Peekskill has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there house rentals with a dedicated workspace in Peekskill?
Yes! Work meets play with ease at over 10 house rentals in Peekskill featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Peekskill?
Experience the best of Peekskill with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Peekskill?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Where should I stay in Peekskill?
Make yourself at home in Peekskill by choosing from our most frequently booked neighborhoods. We have over 120 vacation rentals in Peekskill, and over 50 vacation rentals in Pleasantside.
Do house rentals in Peekskill have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Peekskill. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Peekskill?
Four-legged friends are welcome in Peekskill. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Peekskill have free parking?
Absolutely! We offer over 20 house rentals with free parking in Peekskill. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Peekskill have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Peekskill. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Peekskill have wifi?
Absolutely! We offer over 20 house rentals with wifi in Peekskill. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Peekskill

Total vacation rentals
Explore 20 vacation rentals in Peekskill

Nightly prices starting at
Peekskill vacation rentals start at $60 per night before taxes and fees

Verified guest reviews
Over 1,580 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Peekskill vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Peekskill rentals

4.8 Average rating
Peekskill stays are highly rated by guests—averaging 4.8 out of 5!
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